William W. Willingham, a pioneer settler of Kissimmee Island, Florida, was a cattle baron, whose character was flawed by a love of liquor and a reckless, bullying, brutal and revengeful disposition which led to his becoming an infamous desperado.

William W. Willingham, nicknamed "Bill" or "Bill Ham," was born January 25, 1842 in Ware County, Georgia. With his parents, William Henry and Anna E. (Hilliard) Willingham, Bill moved before 1845 to Columbia County, Florida, and thence about 1848 to the Alafia settlement, near the present site of Mulberry, where his father engaged in cattle ranching. In October 1858, William H. Willingham exchanged his property in Alafia for a stock of cattle and pasture rights on Chloroform Branch at Kissimmee Island, a large range located in the Kissimmee River Valley. In 1862, William H. owned 1,550 head of cattle.

During the Civil War, William W. enlisted at Fort Brooke as a private on May 27, 1862 in Company K, 8th Florida Infantry, CSA. At Gettysburg on July 2, 1863, he was wounded by a lead ball in the left foot and captured. Paroled at Baltimore September 25, 1863, he was allowed to return home on furlough, at the expiration of which time he enlisted at Fort Meade in Capt. F. A. Hendry's Company. During the latter service, he was in 1864 wounded by a lead ball in the right foot and declared incapacitated for duty and returned home.

On July 25, 1866, he married Ann E. Starling, born 1844, Bulloch County, Georgia, daughter of Lucretia Virginia Kirkland and stepdaughter of James Isham Lewis. They were childless. By the marriage Bill acquired brothers-in-law among whom were John Collier, Jr., John Montes de Oca, Jr. and Everett Parker. His extended family also embodied his sisters' husbands which included James Thomas Hancock, Manuel Montes de Oca, William Henry McLaughlin, and Readding Blount Parker.

During the late 1860s, William H. gave his land at Kissimmee Island to Bill and moved to Fort Meade. By 1877, Bill was a large stock owner, worth an estimated $50,000.

On July 23, 1877, Julius C. Rockner, a Fort Meade merchant and cattleman, was shot and killed near Fort Meade while herding cattle near Fort Meade. An unidentified suspect was seen fleeing the scene, and as Rockner and Willingham were engaged in a feud, in which Bill had accused Rockner of cattle rustling, Bill was identified in public opinion as the murderer. On August 31, 1877, Bill and John Montes De Oca were arrested in Polk County and charged with the murder of Rockner. As there was no jail in Polk County, Sheriff R. H. Peeples transported the two to the Tampa prison. John was soon released, while Bill somehow managed to return to Kissimmee Island. As Rockner had killed attorney Hilliard Jones in December of 1875 and was considered a dangerous man, there was little public pressure to arrest Bill. Not until April 1878 was he indicted for the murder. When the trial was eventually held in July 1880, he was acquitted with the courtroom erupting in a perfect roar of cheers for the jury for their verdict.

Previously in August 1879 at Fort Meade, Bill and Morgan Snow had engaged in a fight with pocket knives, with both men seriously injured but due to the skill of Dr. C. L. Mitchell both
recovered. An old grudge of unknown origin and pop-skull whiskey was blamed for the affray.

On September 4, 1880, Bill approached the Peace River ferry (owned by his father) at Fort Meade, and, not finding William McLaughlin, the ferryman and his brother-in-law, attempted to paddle a boat across the swollen river, but fell into the water and nearly drowned. Pulled into a flat, Bill seized McLaughlin by the collar and fired at him. In defense, McLaughlin stooped down and threw Bill by his feet into the river again. As Bill was clinging to the flat and climbing in, McLaughlin stooped down to pick up a pole, but Bill, believing that he was to be knocked back into the river and left to drown, fired and McLaughlin, wounded, jumped overboard. McLaughlin, subsequently, died on September 12, 1880. Bill returned to the safety of Kissimmee Island where he was able to evade attempts to capture him by hiding in the swamps. In Bartow on October 6, 1883, a $500-reward was publicly announced for the arrest and conviction of the murderer of William McLaughlin.

In April 1884, Bill went aboard Capt. John Pearce's steamboat on the Kissimmee River. The circumstances of how he was captured varied considerably. Capt. Pearce reported that Bill, upon a slight provocation, threatened to kill him, and in defense he knocked the desperado down and then stayed with him until he saw him safely landed in the Orlando jail. A less heroic account related that Capt. Pearce located Bill at Camp Hammock and with the help of his engineer, Charlie Dudley, got Bill drunk and "tied him up like a hog." Sobered, Bill offered Pearce a bribe of gold but Pearce refused, with the reply, "No, there'd be two of us in the woods then." Polk County Sheriff William Bowen went to Orange County and returned with Bill, who had the dubious distinction of being the first inmate in the new Polk County jail.

In July 1884, the trial of William W. Willingham for the murder of William McLaughlin began in the new unfinished courthouse at Bartow with Judge Henry L. Mitchell of the Sixth Judicial District presiding. S. M. Sparkman, the State's Attorney, assisted by G. W. Hanson, prosecuted the case while E. K. Foster of Sanford and J. B. Wall of Tampa,assisting, were the defense team. A large crowd attended with intense interest manifested due to the defendant's long defiance of the law and fear his money would stay the hand of justice. A further anxiety was whether a jury could be found that would convict a man of murder in the first degree as in sixteen previous trials for murder in Polk County every defendant was acquitted, not withstanding the fact that in most of the cases the evidence was deemed sufficient to convict. The principal witnesses for the prosecution were Dr. C. L. Mitchell, the attending physician, and two Negroes, Bob Williams and Henry Wells, who were present at the time of the shooting. The evidence of the shooting by the defendant was so strong that the only defense that could in reason be made was the plea of temporary insanity or drunkenness, of which there was no evidence. The jury brought in a verdict of guilty of murder in the first degree, with recommendation of mercy. Willingham was sentenced to life imprisonment at hard labor in the state penitentiary.

While Bill was in prison, his wife, Ann E. Willingham, on May 5, 1886 sold to Ziba King a large stock of cattle and other personal property owned by Bill, which action he contested, but lost. They were subsequently divorced on November 16, 1893 and Ann later married Richard Smith of Kissimmee.

At the time Florida leased convicts to the highest bidders. While at a turpentine farm near Live Oak, Bill became obsessed with escaping. In one such endeavor, he climbed over the stockade wall but was overtaken about one-half mile from the prison. On another occasion in February 1889, a guard fired at him, shattering his left arm from the elbow down, which ended his escape attempts. Bill engaged at great expense prominent attorneys to appeal his conviction and when the efforts failed, to seek a pardon. In April 1898, Thomas L. Wilson of Wilson & Wilson went to Tallahasee and presented petitions for his pardon signed by more than a 1,000 citizens with the result he was formally pardoned on May 23, 1898. The "pardon" document specified that his release was conditioned upon "totally abstaining from the use of intoxicating liquors and lead an orderly and law abiding life; failing which this release to be annulled, and he to be returned to the State Prison."

On May 31, 1898, Bill arrived in Bartow and then proceeded to the home of his aged mother at Fort Meade. Blaming whiskey for much of the troubles of men, he vowed never again to drink and to live peaceably and to serve God for the remainder of his days; however, some judged him unreformed. Bill, his fortune gone, retired to a small place in Kissimmee Island. A number of old timers gave him a small stock from their herds, and he, began anew. In November 1909, his assets included three horses and seventy-five cattle, valued at $700.

On May 26, 1908, W. W. Willingham of Arbuckle, Polk County applied for a Confederate pension from his service in Capt. Hendry's Co. due to being permanently disabled by reason of wounds received in service. On June 1, 1908, George W. Hendry of Bartow and Benjamin F. Blount of Eagle Lake gave a joint affidavit that they had served with W. W. Willingham in Capt. Hendry's Co. His claim was approved December 23, 1908 as pensioner no. 7439 with pay from June 4, 1908 at the rate of $120 per annum. Under the Act of 1909, he reapplied on November 3, 1909. W. H. Lewis and N. C. Langford attested to his application. On March 8, 1910, the Board of Pensions repudiated the twice-wounded veteran by disallowing his pension claim as a War Department record showed he was last on the rolls of Co. K as absent without leave since October 31, 1863, ignoring his proven service in Capt. Hendry's Co.

William W. Willingham died on June 6, 1910. Burial was in Pleasant Grove Cemetery, Fort Meade.

His obituary in the Fort Meade Leader of June 9, 1910 stated:

"William Willingham, A picturesque character-
"Gone from among us.
"In the death of William Willingham, which occurred this week, Polk County loses its most picturesque character. With his life closed a career as interesting as that of Jesse James.
"A murerer of four men, the possessor of an immense fortune in cattle, he remained unmolested on his plantation nearr the Kissimmee river through the sheer force of his daring, in spite of warrants for his arreswt, until, lured onto a Kissimmee river boat and getting intoxicated, he was captured by a supposed friend, and after a trial which stirred the county to its borders, he was convicted of murder in the first degree and sentenced to prison for life. Effort after effort was made by his mother and some influential friends for his pardon but this was not affective until about sixteen years time had been served then only on condition that he abstain from fiery beverage which had been his undoing.
Emerging from the penitentiary without a dollar he began life all over again and by his industrious efforts he had begun to build up another fortune when death stepped in. It was a curious fate that he who had dared death so often to bullets should be the victim of disease at last."